milestones
Year
Milestone
 
Raised in Woodside, Queens and Valley Stream, NY
 
Worked as a production assistant and van driver for "Entertainment Tonight" until January 1995
1994 
Shot first feature, "The Brothers McMullen" over the course of eight months
1995 
After winning the Grand Prize at Sundance, sold the film to 20th Century Fox's Searchlight Pictures
1996 
Helmed second feature, "She's the One"; also scripted and starred
 
Formed Irish Twin Productions and signed a two-year development deal with Fox Television
1998 
Directed and wrote third feature, the romantic comedy "No Looking Back"
1998 
Co-starred with Tom Hanks in Steven Spielberg's "Saving Private Ryan"
2001 
Played a cop alongside Robert De Niro in "15 Minutes"
2001 
With brother Brian, executive produced the NBC sitcom "The Fighting Fitzgeralds"
2001 
Wrote, directed and starred in the romantic comedy "Sidewalks of New York"
2002 
Wrote an episode for the HBO drama series "The Wire"; episode was nominated for an NAACP Image Award
2003 
Starred as a con artist in the drama "Confidence"
2004 
Premiered "Looking for Kitty" at the Tribeca Film Festiva; produced, directed and co-starred (released in 2006)
2005 
Played a love interest for Grace (Debra Messing) on NBC's "Will & Grace"
2006 
Played himself in several episodes of the HBO series "Entourage" where he works with Johnny Drama on a new series
2006 
Wrote, directed and co-starred as an apprehensive groom in "The Groomsmen"
2007 
Helmed the romantic comedy, "Purple Violets," in which he co-starred with Debra Messing and Patrick Wilson; first feature film to be released and distributed by iTunes
2008 
Appeared in the romantic comedy, "27 Dresses"
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Lauren and Heidi of MTV's "The Hills"
Jeff Lipsky/MTV

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